Details
| Stereochemistry | MIXED |
| Molecular Formula | C11H16N8O8 |
| Molecular Weight | 388.2935 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 0 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OCN1C(NC(=O)NCNC(=O)NC2N(CO)C(=O)NC2=O)C(=O)NC1=O
InChI
InChIKey=ZCTXEAQXZGPWFG-UHFFFAOYSA-N
InChI=1S/C11H16N8O8/c20-2-18-4(6(22)16-10(18)26)14-8(24)12-1-13-9(25)15-5-7(23)17-11(27)19(5)3-21/h4-5,20-21H,1-3H2,(H2,12,14,24)(H2,13,15,25)(H,16,22,26)(H,17,23,27)
| Molecular Formula | C11H16N8O8 |
| Molecular Weight | 388.2935 |
| Charge | 0 |
| Count |
|
| Stereochemistry | MIXED |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/imidazolidinylurea_508.pdfCurator's Comment: Description was created based on several sources, including http://www.excipientsguide.com/excipient_details.aspx?Id=51 and http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/019927s028lbl.pdf
Sources: https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/imidazolidinylurea_508.pdf
Curator's Comment: Description was created based on several sources, including http://www.excipientsguide.com/excipient_details.aspx?Id=51 and http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/019927s028lbl.pdf
Imidurea (Imidazolidinyl urea) is used as an antimicrobial agent and preservative in cosmetics and toiletries. It is very active against gram and gram- bacteria as a synergist in combination with parabens. Imidazolidinyl urea is more active against bacteria than fungi and is often combined with parabens to provide a broad spectrum preservative system. This preservative is one of the most widely used preservative systems in the world. The Food and Drug Administration (FDA) considers imidazolidinyl urea as one of the most common antimicrobial agents used in cosmetics. Due to its high water solubility, imidazolidinyl urea can be incorporated into almost all water-based cosmetics, toiletries, and cold mix formulations. It is present in a wide range of liquid and powder products such as baby lotion, skin cream, sunscreens, shampoos, eyeliners, blush, perfumes, deodorants, hair dyes, shaving cream, and face masks. Imidazolidinyl urea is permitted for use in personal care products in the European Union at a maximum concentration of 0.6%. In Japan, imidazolidinyl urea is allowed in rinse-off cosmetics such as shampoo, body wash, and facial cleanser at a maximum concentration of 0.3%. Imidurea is an ingredient of FDA-approved NIZORAL® (ketoconazole) 2% Shampoo, indicated for the treatment of tinea (pityriasis) versicolor caused by or presumed to be caused by Pityrosporum orbiculare (also known as Malassezia furfur or M. orbiculare).
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2364156 Sources: http://www.ncbi.nlm.nih.gov/pubmed/26319029 |
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Target ID: Pseudomonas aeruginosa growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/19921329 |
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Target ID: Staphylococcus aureus growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/19921329 |
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Target ID: map04210 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11853695 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | Nizoral® (ketoconazole) 2% Shampoo Approved UseNIZORAL® (ketoconazole) 2% Shampoo is indicated for the treatment of tinea (pityriasis) versicolor caused by or presumed to be caused by Pityrosporum orbiculare (also known as Malassezia furfur or M. orbiculare). Launch Date1990 |
Doses
| Dose | Population | Adverse events |
|---|---|---|
600 ug/m2 single, topical Highest studied dose Dose: 600 ug/m2 Route: topical Route: single Dose: 600 ug/m2 Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Other AEs: Eczema... |
2 % single, topical Studied dose |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Other AEs: Contact dematitis... |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Eczema | 2% | 600 ug/m2 single, topical Highest studied dose Dose: 600 ug/m2 Route: topical Route: single Dose: 600 ug/m2 Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Contact dematitis | 2 % single, topical Studied dose |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Chemical allergens stimulate human epidermal keratinocytes to produce lymphangiogenic vascular endothelial growth factor. | 2015-03-01 |
|
| Differentiation of skin sensitizers from irritant chemicals by interleukin-1α and macrophage inflammatory protein-2 in murine keratinocytes. | 2013-01-10 |
|
| B cell increases and ex vivo IL-2 production as secondary endpoints for the detection of sensitizers in non-radioisotopic local lymph node assay using flow cytometry. | 2012-03-25 |
|
| The intra- and inter-laboratory reproducibility and predictivity of the KeratinoSens assay to predict skin sensitizers in vitro: results of a ring-study in five laboratories. | 2011-04 |
|
| Use of IL-8 release and p38 MAPK activation in THP-1 cells to identify allergens and to assess their potency in vitro. | 2010-09 |
|
| [Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations]. | 2004-05 |
|
| Developing a dynamic pharmacophore model for HIV-1 integrase. | 2000-06-01 |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Imidurea is an ingredient of NIZORAL® (ketoconazole) 2% Shampoo
Apply the shampoo to the damp skin of the affected area and a wide margin surrounding this area. Lather, leave in place for 5 minutes, and then rinse off with water. One application of the shampoo should be sufficient.
Route of Administration:
Topical
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/26319029
30 ug/ml of Imidurea increased IL8 release and CD86 expression in THP-1 cells
| Substance Class |
Chemical
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M629807ATL
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N0000185508
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C45678
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CONCEPT | Industrial Aid | ||
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SUB23453
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1368885
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CHEMBL65433
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M629807ATL
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C65895
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1336806
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N0000175629
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PRIMARY | Increased Histamine Release [PE] | ||
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51805
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IMIDAZOLIDINYL UREA
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m6227
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N0000171131
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N0000184306
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PRIMARY | Cell-mediated Immunity [PE] | ||
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M629807ATL
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ACTIVE MOIETY |